Diisopropylethylamine → HCID 118308243, compound

HRID 1750540Notes

Reaction equation

HRID 1750540 reaction equation
Cl[C:2]1[CH:7]=[N:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[NH2:12][C@H:13]1[CH2:17][CH2:16][CH2:15][C@@H:14]1[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22].CCN(C(C)C)C(C)C>CS(C)=O>[F:9][C:8]([F:11])([F:10])[C:5]1[N:6]=[CH:7][C:2]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 17040218(1S,2S)-trans-N-Boc-1,2-cyclopentanediamineHCID 189876452-Chloro-5-(trifluoromethyl)pyrazine

Product 1

HCID 118308243HCID 118308243, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

A solution of 2-chloro-5-(trifluoromethyl)pyrazine (CAS number 799557-87-2; 2.0 g, 10.98 mmol), tert-butyl N-[(1S,2S)-2-aminocyclopentyl]carbamate (CAS number 586961-34-4; 2 g, 9.99 mmol) and DIPEA (5.23 ml, 30.0 mmol) in DMSO (20 ml) was sealed and heated at 140° C. for 3 hours. The reaction mixture was partitioned between ethyl acetate (200 ml) and water (100 ml). The organics were washed with water (2×100 ml), brine (100 ml), dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica, 10-40% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (200 ml) and water (100 ml)
  2. washThe organics were washed with water (2×100 ml), brine (100 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica, 10-40% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-5419bf54d7664a518bf921ad7d35448d
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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